U.S. Pat. No. 3,907,779 issued Sept. 23, 1975 describes and claims the compound 1-(2-deoxy-.beta.-D-ribofuranosyl)-5-methyl-5,6-dihydro-s-triazine-2,4-(1H ,3H)-dione and various derivatives thereof.
U.S. Pat. No. 3,907,779 describes the original discovery, identification, and production of 1-(2-deoxy-.beta.-D-ribofuranosyl)-5-methyl-5,6-dihydro-s-triazine-2,4-(1H ,3H)-dione by the controlled fermentation of the microorganism Streptomyces platensis var. clarensis, NRRL 8035.
The novel compounds of this invention have not been produced by the controlled fermentation of the microorganism NRRL 8035, and it is not clear how this objective might be accomplished with the microorganism.
U.S. Pat. No. 3,708,469 issued Jan. 2, 1973 describes the silylation extension of the Hilbert-Johnson reaction for the production of 2-thiopyrimidine nucleosides. Winkley and Robins, J. Org. Chem. 35, pp. 491-496 (1970) utilized the bis-trimethylsilyl derivative of 4-amino-s-triazine-2-(1H)-one for reaction with blocked ribofuranosyl halides.
In this invention, the Hilbert-Johnson reaction is modified to the use of the mono-silylated or disilylated 5,6-dihydro-s-triazines which are non-aromatic, and an optimal temperature range between minus (-) 25.degree. C. and 25.degree. C. is disclosed. None of the prior art references disclose a silylated non-aromatic sym-triazinone base for reaction with a blocked-pentofuranosyl halide. More specifically, none of the prior art references disclose the use of a monosilylated non-aromatic sym-triazinone base for this reaction.